


Paved with Good Intentions

by GracieAnneJackson



Series: Sister Christian [9]
Category: Supernatural
Genre: Aftermath of Torture, American Sign Language, Blood and Gore, Blood and Injury, Blood and Torture, Blood and Violence, Canonical Character Death, Character Death, Character Death Fix, Dark, Dark Dean Winchester, Deaf Character, Death, Emotional Hurt/Comfort, Emotionally Hurt Dean Winchester, F/M, Going to Hell, Hell, Hell Trauma, Hellhounds, Hurt Dean Winchester, I'm Going to Hell, Injury, Major Character Injury, Minor Character Death, Mythology References, No Sex, No Smut, Non-Sexual Bondage, Non-Sexual Submission, Past Torture, Plot, Protective Dean Winchester, Psychological Torture, Restraints, Screenplay/Script Format, Service Submission, Sick Dean Winchester, Submission, This Is Not Going To Go The Way You Think, Torture, Tortured Dean Winchester
Language: English
Status: Completed
Published: 2019-04-16
Updated: 2019-04-16
Packaged: 2020-01-14 20:19:07
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 1
Words: 6,540
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18483634
Author URL: https://archiveofourown.org/users/GracieAnneJackson/pseuds/GracieAnneJackson
Summary: The rescue mission to get Joan out of hell starts off sideways and only gets worse. An old friend tries to help - is it too little, too late?





	Paved with Good Intentions

**Author's Note:**

> Hey, y'all.
> 
> Full disclosure: shit gets dark this go 'round. Scary and triggering themes, torture, blood and gore at the TV Mature level. I didn't want to surprise anyone with that.
> 
> If you're just now stumbling onto this series and you're wondering what the heck is going on, try starting at Episode 1: Sister Christian.

**FADE IN:**

**EXT. HELL BEACH - NIGHT**

The hell side of the portal is vertical, standing independently in the middle of a rocky beach. The ground is made of small, smooth stones, and toward the water we see immense, craggy boulders with waves crashing against them. The sea spray seems to freeze before it hits the ground. An unnaturally curved crescent moon overhead and the red glow of the portal are the only light, leaving the water looking black.

SAM, DEAN, KETCH and CASTIEL come flying out of the portal at falling speed, too fast to catch their balance. All four are sent sprawling. DEAN vocalizes in pain, struggling to right himself. SAM helps him up.

The four men look around to get their bearings, zipping their jackets and pulling on warm hats. Their breath is visible.

KETCH

Well, this isn’t so bad. A bit brisk is all.

CASTIEL

Oceanus. This is the outermost border of hell. The palace, where I expect to find Joan... it’s a long way from here.

DEAN

Well, let’s get a move on, then.

A long-necked, reptilian SEA MONSTER is suddenly visible behind the rocks, about 30 feet away. It growls like a dragon, turning its glowing eyes toward the four men.

SAM

MOVE!

The four sprint away from the water, DEAN limping slightly. The SEA MONSTER huffs a breath of steamy air, stretching its neck out toward them, but lets them go.

 

**INT. HELL’S TOP FLOOR OFFICE – NIGHT**

We see a richly furnished, but modern executive office suite with windows overlooking the dark, hellish landscape. It seems to be about thirty floors up. A heavy, ornate desk and matching bookshelves occupy the main space in the office. A fancy pen set and a black telephone are the only items on the desk. In another corner, a sort of dentist’s chair with a few side tables is set up.

JESSE walks in and removes his coat, hanging it on a hook near the door. He rolls up his sleeves.

A knock is heard at the door.

JESSE

Come in.

Three DEMONS enter. Two of them hold JOAN’s body, and another holds a red box, similar to those used by the British monarchy. The DEMON holding the box stands ceremoniously by the desk. Jesse motions to the dentist’s chair.

JESSE

Over there.

The two demons roughly drop JOAN’s body onto the chair, causing JESSE to snap impatiently.

JESSE

Gently!

The demons sheepishly straighten JOAN’s clothes and bring her legs up onto the footrests. They bow deeply and hurry out of the room.

JESSE turns to the third demon and produces a gold key from his pocket. When he opens a red box, a light shines out of it, causing JESSE to avert his eyes in displeasure.

JESSE

Obnoxious.

JESSE picks up a pair of blacksmithing tongs from the desk. He uses them to retrieve a glowing orb from the box. It shines brightly and the demon holding the box must avert his gaze. JESSE brings the orb to JOAN’s body and drops it on her chest. The orb slowly disappears inside JOAN’s body.

After a moment, JOAN sits bolt upright and takes a huge, desperate gulp of air. Immediately, wrist and ankle restraints emerge from the dentist’s chair and restrain JOAN. She screams in frustration. A lap belt then emerges and slams her back into the chair, followed by a belt across her forehead.

JOAN

Son of a bitch!

JOAN casts her gaze about with her limited range of movement. She sees JESSE, who wordlessly dismisses the DEMON holding the box. The DEMON exits.

JOAN

You. What did you do to me? Where am I?

JESSE

So glad to see you’ve awakened. Welcome to hell. The good news is, you’re not dead. You’re welcome.

JOAN

Bite me.

JESSE chuckles, examining the blacksmith’s tongs in his hands. He walks toward JOAN.

JESSE

The bad news is, as long as you’re here, you can’t die.

JESSE abruptly brings the tongs down hard across JOAN’s right leg, just below the knee. We hear a sickening crack and her leg bends unnaturally. JOAN screams in pain.

 

**EXT. PERSEPHONE’S GROVE - NIGHT**

SAM, DEAN, KETCH and CASTIEL run off the beach, but come to a halt just within the tree line. The forest is dark and jungle-like, with enormous trees that give the impression of being centuries old at least. A small, overgrown path leads from the beach into the trees.

The team stops to catch their breath, leaning against the trees. Only CASTIEL seems unaffected.

KETCH

So, Castiel. What sort of landscape should we expect, here? Milton? Dante?

CASTIEL

Milton, no. He was just a poet. And he was blind anyway. Dante really was led through hell, but spent most of his time in Tartarus, which I am very much hoping we will not be visiting.

SAM

Tartarus?? You don’t mean –

CASTIEL

Yes, Virgil was actually the closest on the general layout. Unsurprising, since at that time the borders between worlds were thinner. Several living humans actually found themselves on the wrong side.

KETCH and SAM seem intimidated. DEAN is annoyed.

DEAN

What the hell are you guys talking about?

SAM grins mirthlessly. KETCH doesn’t answer, just covers his face with his palm.

CASTIEL

They were asking about the myths of what hell is really like.

DEAN

Well. I don’t need to. I’ve been here before.

CASTIEL

I remember. The last time I was here was with a legion of angels, to pull you out. You were in the deepest pit of Tartarus – Limbo. Not far from where Sam spent time in the cage.

Beat. SAM swallows, remembering. KETCH straightens and seems to lose his air of superiority.

CASTIEL

But as I said, I don’t expect that we will be going there. Jesse would likely take Joan to the palace.

SAM

Where are we now?

CASTIEL

Some called it Persephone’s grove. Persephone, of course, has long since left.

We see the group from a handheld camera, peering through the trees. We hear ragged, animal breathing.

CASTIEL

We need to keep heading away from the beach. We’re looking for a marsh.

A rustle from the trees alerts the team to the presence of whatever that was. They prepare for a fight. SAM draws the demon knife, DEAN draws Joan’s sword, and CASTIEL and KETCH draw angel blades.

More rustling, this time behind the group, forces them onto the path. They form a circle, backs to each other. A low growl is heard. KETCH’s eyes widen.

KETCH

Hellhounds! Run!

The four run along the path, through the trees. They hear the dogs behind them, at a distance. Suddenly, they come on a ravine. A bridge was formerly laid across the gorge, but it has fallen. KETCH and SAM stop abruptly at the precipice; DEAN and CAS almost run into them, but stop just in time. A howl is heard in the middle distance.

A wooden ladder thunks into place at SAM’s feet, leading down into the dark ravine. A woman’s voice calls from the ravine, but we see no one.

WOMAN

Get down here! Quick!

Another howl – closer this time. SAM looks at the others. They nod grimly. SAM climbs down the ladder, followed by CASTIEL, DEAN, and then KETCH. The ladder is taken down. Silence.

Then, two huge hellhounds emerge from the woods. They are fully visible – black, mangy dogs with glowing eyes. They sniff the precipice of the ravine, investigating. They take off running along the edge of the gorge, howling.

The team crouches in the bottom of the deep gorge, shrouded in darkness. When the hellhounds leave, they begin to take stock of their surroundings. KETCH produces a flashlight. We see SAM, DEAN, and CASTIEL – muddy, but unharmed. A pale hand appears from the darkness and is placed on KETCH’s shoulder. He freezes, then turns slowly, shining the flashlight at their rescuer.

It is EILEEN LEAHY. SAM immediately embraces her. She bear hugs him back. DEAN then embraces her.

Lines in American Sign Language (ASL) are accompanied by subtitles.

SAM

(ASL) What are you doing here?

EILEEN

(ASL) I’ve been here since I died. I was killed by a hellhound, who dragged me down here. But there was no contract; nowhere to drag my soul. So I’ve been wandering the plains. The hounds have been after me this whole time, trying to drag me back to where they keep the other lost souls. But I’ve gotten good at outsmarting them.

CASTIEL

(Spoken) I don’t understand. Why would a hellhound collect you if there were no contract on your soul?

KETCH shifts uneasily and clears his throat. Everyone stares at him.

SAM

(Spoken) You... bastard.

KETCH

(Spoken, to EILEEN) I’m sorry. I’m not that person anymore. I was just doing my –

EILEEN punches KETCH squarely on the jaw and he stumbles against the wall of the ravine. He stands, holding his face, but does not retaliate. SAM and DEAN smile.

KETCH

(Spoken) Well deserved.

EILEEN

(ASL, to SAM) What are you doing here?

SAM

(ASL) We’re looking for a friend. We think she’s in the palace.

EILEEN

(ASL) That’s across the river. I’ve never been there. But I can get you to the boats.

DEAN cuts in, waving for attention.

DEAN

(ASL) No. Go to the beach. There’s a portal there. Our people are on the other side. You’ll be safe.

EILEEN smiles and pats DEAN’s shoulder kindly.

EILEEN

(ASL) I’m dead, Dean. My body is long buried. There’s no going back. I’m only here as my soul. But my soul needs to get out. I don’t belong here.

The four are sad to hear this. But SAM is determined.

SAM

(ASL) Then we’ll get you out. Go to the portal.

EILEEN

(ASL) I’m going to get you to the river. Then I’ll head to the beach.

SAM and DEAN nod. EILEEN takes the flashlight from KETCH and leads them along the bottom of the ravine. The rest fall in line, KETCH in the back.

 

**EXT. STYX RIVERBANK - NIGHT**

SAM, DEAN, CASTIEL, KETCH and EILEEN advance through some thick brush as cover. The area is covered in fog. We see a line of boats parked by the bank of a slow-moving river. Just beyond the boats, there is a large fenced area. About 100 people are in the fenced prison compound, sitting or standing around. The outside of the fence is patrolled by fully visible hellhounds and several skeletal, wraith-like figures.

EILEEN

(ASL) There are the boats. This is as far as I can take you.

SAM

(ASL) What are those things?

EILEEN

(ASL) That’s where I’m supposed to be. They’re souls that don’t belong here. Just got dragged in at some point and now they’re stuck.

SAM

(ASL) I mean the monsters guarding them.

EILEEN

(ASL) I don’t know.

DEAN

(ASL) Demons.

SAM and EILEEN look at DEAN in disbelief. CASTIEL nods in agreement.

CASTIEL

(Whisper) They’re demons with no vessels. On Earth they appear as clouds of smoke, but here, even humans can see their true faces.

KETCH

(Whisper) All right. In this fog, we can get a boat and be on our way without alerting the guards. (To EILEEN) Go to the beach, lass. There is a portal there. Leave this place.

EILEEN nods, embracing SAM and DEAN in turn. As EILEEN turns to make her way back through the brush, the two HELLHOUNDS jump out at them, snarling. ONE takes hold of EILEEN’s jacket and begins to drag her toward the prison.

SAM, DEAN, CASTIEL and KETCH draw their weapons and begin to fight the HELLHOUNDS off. SAM, DEAN, and KETCH team up on the nearest HELLHOUND.

CASTIEL attacks the one dragging EILEEN away, but the creature turns and forces CASTIEL to the ground. CASTIEL drops his angel blade. EILEEN picks it up and stabs the HELLHOUND with it, but does not kill it. CASTIEL uses the opportunity to smite the creature instead.

SAM, DEAN and KETCH manage to kill the other HELLHOUND together, but SAM has a big scratch across his jaw.

The commotion draws the attention of those guarding the prison. The team, peering out from their cover, see the prison guard DEMONS and HELLHOUNDS coming their way to investigate.

KETCH turns to the team and takes off his backpack.

KETCH

Give Joan my regards. (To EILEEN) I... I’m sorry. I hope you can find peace.

With that, before anyone can stop him, KETCH takes off across the open area at a sprint. He heads for the trees, running away from the river. All of the DEMONS and HELLHOUNDS from the prison follow after him, leaving no hostiles in the path of the team.

SAM, DEAN, CASTIEL and EILEEN only stare in shock for a moment.

DEAN

Goddammit. Haven’t we lost enough people?

EILEEN

(Spoken) It doesn’t halfway redeem him from a lifetime of murder. But it does give us a shot.

EILEEN runs to the prison and uses CASTIEL’s angel blade to break open the lock on the fence. She addresses the PRISONERS in the compound.

EILEEN

Come on, we’re getting out of here! Head for the beach!

As the PRISONERS file out, she embraces SAM one last time, then kisses him.

EILEEN

(ASL) Good luck, Sam.

SAM

(ASL) You, too.

EILEEN offers the angel blade back to CASTIEL, but he shakes his head.

CASTIEL

(ASL) Keep it. You may need it.

EILEEN

(ASL) Thank you.

EILEEN joins the group of prisoners running toward the beach. SAM watches her for a while before turning to help CASTIEL put one of the boats in the water.

DEAN walks back into the brush to get Ketch’s backpack. He glances back to make sure CASTIEL and SAM aren’t watching, then lifts his shirt to check his wound. It seems bigger, its tendrils reaching further past his belt and across his back and chest. It’s turned a deeper red, and has again soaked through the cotton gauze dressing. He lowers the shirt again, grabs the pack and walks back to the others, trying to hide his pain.

SAM, DEAN and CASTIEL push the boat into the water and climb in. They produce oars from the bottom and begin to row away from the riverbank, into a thick fog, where they disappear from sight.

 

**INT. HELL’S TOP FLOOR OFFICE – NIGHT**

Cold water splashes on JOAN’s face, waking her up. She is still restrained on the dentist’s chair in JESSE’s office. We see JESSE standing over her, holding a cup.

JESSE

There. You’ve really got to stop passing out all the time. Now, where were we?

We see that her skin at several of her warding tattoos has been sliced open in an “x”, destroying the sigils. She has been badly beaten, and some of her wounds look like they have begun to heal. JOAN takes a deep breath and closes her eyes, trying to relax.

JESSE picks a knife up from the side table, where several instruments of torture are laid out.

JESSE

Ah, yes. Day... six? Seven? I’ve lost count. You were about to unconditionally submit your very being to my will.

JOAN

(Calmly) Bite me.

A DEMON enters the room without knocking, but then bows deeply.

JESSE

I am not to be disturbed.

DEMON

Apologies, your majesty, er, your grace, uh...

JESSE

What do you want.

DEMON

There is a disruption across the river, sire. The unburied souls are loose.

JESSE

What do I care? Send some hellhounds to round them up.

DEMON

They’re headed for the portal, sire. The beach. And...

JESSE

Spit it out.

DEMON

One of the hounds was... smitten, sire. Smited? Smote? The work of an angel, we suspect.

JESSE looks at JOAN in surprise.

JESSE

Well. That was fast. It seems we won’t have time to really get to know each other. I’ll have to speed this process up a bit.

JESSE crosses to the desk and presses a button on the telephone.

JESSE

Obizuth, would you join us, please?

Almost immediately, a strikingly beautiful blonde woman appears, wearing a black suit. She blinks, and shows her completely white eyes.

OBIZUTH

I thought you’d never ask.

JESSE

I have something else to attend to, and I’m afraid our deadline on Joan here as been moved up. Would you take care of it?

OBIZUTH

Any limits I should be aware of?

JESSE

No. Just a pressing time constraint.

OBIZUTH bows deeply.

OBIZUTH

That shouldn’t be a problem. I’ll take her downstairs.

OBIZUTH crosses to JOAN and places a hand on her shoulder. They vanish.

 

**THE RIVER STYX – NIGHT**

DEAN, SAM and CASTIEL row across the river Styx. It is more of a swamp, and in some places SAM uses the oar to push off the muddy bottom. A thick layer of fog reduces visibility to near zero.

DEAN

Cas. Are you sure we’re heading in the right direction? I can’t see anything.

CASTIEL

I’m fairly sure. We shouldn’t be far now.

A deep growl is heard. At first, it sounds like thunder, but then it is clear that it comes from a beast.

DEAN

(Whisper) Sea monster?

SAM

(Whisper) Can’t be. It’s too shallow.

The growl is heard again. This time, all three men slowly turn in terror to see two glowing, red eyes through the fog. Then four. Then six. The fog disperses slightly, revealing CERBERUS, a twenty-foot-tall, three-headed hellhound about 100 feet away.

DEAN

What the hell.

SAM

Cerberus?!?

CASTIEL

I wasn’t sure he was still down here. Dean, you have what we talked about?

DEAN reaches into one of the backpacks and retrieves four store-bought pies.

DEAN

Yeah. I just grabbed some random flavors.

CASTIEL

Any honey, mead, or barley?

DEAN

Uh. No. I’ve got apple, pecan, cherry, and... rhubarb.

CASTIEL

It’ll have to do.

SAM rows from the back of the boat, approaching CERBERUS slowly. The beast wears thick chains around each neck, which are anchored in a giant slab. He stands between the river and a hill, which we can’t see over yet. An enormous doghouse stands to one side, with CERBERUS’s name engraved over the door. A giant food bowl is also seen, with several skeletons thrown over the rim.

As SAM pulls them in close to the shore, CERBERUS growls and pulls against his chains. DEAN and CASTIEL raise the pies up in the air and CERBERUS stops growling, instead pulling against his collar to sniff the treats.

DEAN

Okay, Clifford. We’ve got some treats for ya. Okay?

CERBERUS’s attitude changes. He sits down, his three tongues hanging out, ready for his pies. SAM brings the boat to the shore. DEAN and CASTIEL climb out warily, still holding the pies.

SAM gathers their things and begins to make his way out of the boat. He notices an empty boat parked right next to theirs, and sees something on the seat. He picks it up. It is an ornate bracelet.

DEAN and CASTIEL come to the concrete slab where CERBERUS sits and slide the pies within his reach. CERBERUS begins devouring the pies, allowing the three men to run up the hill to safety.

They reach the top of the hill and can take in the landscape. With CERBERUS behind them, a great, dimly lit field of white wildflowers stretches before them, crowded with grayed-out, ashen people in tattered clothes. They stand perfectly still, staring blankly into space.

SAM, DEAN and CASTIEL get their bearings. SAM is in awe. DEAN is freaked out. CASTIEL seems saddened.

DEAN

Don’t tell me. Another thing that Sam’s read about.

SAM

Yeah. The Fields of Asphodel.

DEAN

Oh. Yeah. Of course.

SAM

There’s something else.

SAM holds up the bracelet.

SAM

This was in the other boat down there.

CASTIEL takes the bracelet from SAM and looks at it closely.

CASTIEL

It’s Rowena’s. They’re ahead of us.

 

**THE PITS OF HELL – NIGHT**

We see a dingy, freezing room with stone walls and floors. A large table is in the middle of the room. It is the same room as the one we saw in DEAN’s dream in episode 2 of this season, where ALASTAIR tormented him.

JOAN is upright, facing the table. She is chained to the ceiling by her wrists, her toes just barely able to scrape the floor. Her obviously broken right leg is purple and mottled, and hangs awkwardly. She is shivering and her breath is visible.

OBIZUTH enters with a professional air, carrying a chef’s knife roll. She unrolls it on the table. She inspects her implements as she speaks pleasantly, as if chatting to a friend.

OBIZUTH

So, you’re dating Dean Winchester, right?

JOAN hesitates, but decides to respond.

JOAN

Yes.

OBIZUTH

Small world. I was down here with him, way back when. We were torture buddies.

JOAN stiffens, but says nothing.

OBIZUTH

At first, of course, we were getting tortured together. We died around the same time. But I didn’t make a deal to save my brother. (Chuckles) I just belonged down here, I guess. Anyway, Alastair really did a number on him. Took a long time before he broke. I didn’t. I knew what was good for me. I was torturing other souls within a week. Dean was what, forty years?

JOAN

That’s not possible. Dean’s barely forty years old now.

OBIZUTH

Oh, no, you see, time passes differently here. It would have only been about four months for Earth. And... oh, about eight months in the Palace.

OBIZUTH takes off her suit jacket. Underneath, she is sleeveless, revealing her many scars. She ties up her hair neatly.

OBIZUTH

You’ve only been down here about ten minutes, as far as Jesse is concerned. So don’t worry. We’ll have plenty of time together.

OBIZUTH cuts away JOAN’s shirt, leaving her shivering in a tank top.

JOAN

How long have I been in hell?

OBIZUTH

Total? Earth time? Like three days. So you spent about a week in the palace. But if he had given you to me when you first got here? Sheesh. I’d have had you for a year already. But no use crying over spilled milk.

OBIZUTH eyes JOAN’s remaining tattoos. She spins JOAN as she hangs from her wrists to get a good look. She places a finger on the tattoo on her chest.

OBIZUTH

What’s this one do? oblinto.. potestas... non veneni... can’t quite make it out.

JOAN says nothing.

OBIZUTH

Something about... sealing witchcraft? Come on, spill the tea. I thought we were becoming friends.

OBIZUTH produces a scalpel and begins to cut away JOAN’s witchcraft-suppressing tattoo – and a sizable chunk of flesh with it. JOAN can’t hold in a scream – of both pain and fear. OBIZUTH grows frustrated with how difficult it is to cut it away, so finally, she just grabs the flesh and rips it out of JOAN’s chest. A small squirt of blood gushes out and JOAN almost passes out.

OBIZUTH

No, no, no – can’t have you passing out on me.

OBIZUTH produces a large syringe and injects something into JOAN’s neck.

OBIZUTH

That’ll keep you awake.

JOAN is sobbing in pain. She bites her lip to try and regain control.

JOAN

(Desperate) Why are you doing this? What do you want?

OBIZUTH

Submission.

JOAN

To what? What do you want me to do?

OBIZUTH

Angels need consent. Demons don’t. Jesse, however, requires _submission._ Permanently. Become a vassal of Jesse’s power and will. Feel nothing. Worry about nothing. Cast aside that obnoxious free will and serve Hell. That’s all.

JOAN

He wants to... possess me?

OBIZUTH

(Chuckling) No, no, no. He’s half human. He has a body. He just wants a servant. A loyal, obedient servant. Do you submit?

JOAN takes a deep breath, preparing for what she knows is coming. She whispers something we can’t hear. OBIZUTH leans in close.

OBIZUTH

(Whisper) Do you submit?

JOAN spits blood in OBIZUTH’s face.

JOAN

Bite me.

OBIZUTH calmly wipes the blood from her face and picks up a metal mace from her toolkit.

OBIZUTH

Let’s work on some of your mental barriers, shall we?

OBIZUTH brings the mace down hard against JOAN’s ribs and we hear the sickening crack of breaking bones. JOAN wheezes gasps for air through the sobs.

 

**ASPHODEL MEADOWS – NIGHT**

SAM, DEAN and CASTIEL approach the crowds of gray, zoned-out people. Not one reacts to the three men walking through the fields of thousands of perfectly-still souls.

CASTIEL

Try not to touch any of them. Let them rest.

There is just enough space between each person for the team to go through, single-file – CASTIEL, then DEAN, then SAM. The souls make no eye contact and are perfectly still, except for blinking and shallow breathing.

DEAN inspects one briefly as they pass by.

DEAN

Who are these people, Cas?

CASTIEL

Mediocre souls. Not deserving of an eternity in heaven, nor an eternity of torture. This is what most people think of as purgatory. They’re not in pain. They’re not even bored. They feel nothing.

CASTIEL emerges from the crowd and comes to a road. DEAN comes out behind him. DEAN looks left and in the distance, sees the cavernous, foreboding entrance to a dark tunnel.

DEAN

That’s Tartarus, huh?

CASTIEL

Yes. What most people think of as hell. Level upon level of different torments. Darker as it grows deeper. Last time I was here, I flew into the depths of Tartarus to, how do you put it, “save your ass.”

DEAN

Yup.

DEAN turns around and finds that SAM is not behind him. He is immediately worried.

DEAN

SAM!?

SAM

(O.S., distant) Dean!

DEAN and CASTIEL draw weapons and run toward the sound of Sam’s voice. They find SAM shaking one of the gray souls, trying to slap him awake. DEAN pulls him away from the soul.

CASTIEL

Sam, no, don’t touch the –

CASTIEL stops suddenly when we see that the soul is KETCH. His complexion is washed out, and his clothes and hair are covered in so much ash as to appear gray rather than black.

DEAN

Ketch? Ketch??

KETCH gives no response, only staring out into the blank space before him.

CASTIEL gently leads SAM away.

CASTIEL

He’s in no pain. He’s at rest.

SAM

He died for us, Cas. He led the hounds off so we could get away. Why wouldn’t he be in heaven?

CASTIEL

I wouldn’t presume to know why or how that works.

SAM follows CASTIEL back to the road, followed by DEAN. Their faces are all grim. Turning away from Tartarus, they look up at the palace.

 

**EXT. JESSE’S PALACE – NIGHT**

The PALACE is on a hilltop. The ground before it and around it is black and charred. The art-deco style high-rise itself is made of black stone, and is obscenely expansive. It includes a tower with a large window at the top. A tall, black, stone wall surrounds the building.

SAM, DEAN, and CASTIEL approach the castle stealthily, running between what small cover can be found. They make it inside the wall’s open gate with no resistance, finding a garden with green grass. The three crouch behind a decorative statue in the garden.

SAM

Where is everybody?

DEAN

Maybe Michael already took them all out?

**INT. JESSE’S PALACE – NIGHT**

The three continue to creep inside the building. No one is in the lobby. It looks like an upscale art deco hotel, with several seating areas and a large reception desk. Soft jazz music plays over the intercom. They look around, still expecting a fight.

The intercom music stops and the microphone buzzes to life.

JESSE

(Over intercom) Good evening, gentlemen. You’re a little ahead of schedule, so I hope you don’t mind the delay. I’ll be right down to greet you.

The team grips their weapons tighter, standing back to back to prepare for an attack.

Dozens of un-vesseled, skeletal demons suddenly appear, entering through the walls and floating in midair around the three men. They do not attack.

DEAN

Can you kill something without a body?

SAM

We’re about to find out, I’ve got some angel bullets.

SAM draws a handgun and fires at one of the demons. It flashes orange and explodes. At this, the other demons advance on the team.

JESSE

Stop.

All the demons immediately freeze. JESSE strides into the lobby.

JESSE

Is that any way to treat your hosts?

With a wave of his hand, JESSE sends the sword DEAN was holding, SAM’s demon knife, and SAM’s gun sprawling across the floor, away from the team.

JESSE

It baffles me. How did you think this was going to go differently from last time?

DEAN draws the COLT, pointing it steadily at JESSE. For the first time, JESSE looks nervous.

JESSE

Impressive. I was wondering where that gun had gotten off to. You have my attention, Mr. Winchester.

DEAN

Where’s Joan?

JESSE

Oh, not here. She’s back in your old stomping ground. With my new Grand Torturer. Very, very deep in hell, I’m afraid. Would take you years to mire through there on foot. Perhaps centuries.

DEAN

Let her go!

JESSE

(Calmly) No.

DEAN fires the gun. JESSE deflects the bullet, letting it hit the wall behind him. He turns to look at it, then back to DEAN with disapproval.

JESSE

Now, that was a mistake.

JESSE reaches out his hand and sends DEAN, CASTIEL and SAM to their knees.

JESSE

Apparently, this game will need a round two. But I have so few choices this time. Let’s see. Eenie, meanie, meinie...

MICHAEL

Mo.

MICHAEL is revealed behind JESSE, dressed in full plate armor and carrying an enormous sword engraved with Enochian writing. MICHAEL swings the sword at JESSE, who just barely side-steps it. JESSE shoots a red lightning bolt at MICHAEL, but it bounces off his armor. JESSE steps back.

JESSE

Kill him!

The demons attack, but MICHAEL raises his hand and they all freeze. MICHAEL makes a fist and all the demons are killed simultaneously, crumpling in orange flashes of light.

JESSE, now enraged, uses a lightning attack again.

ROWENA appears behind SAM, DEAN, and CASTIEL, crouched to avoid notice.

CASTIEL

Rowena!

ROWENA

Libertatum impedimentus.

The three can now move again. They scramble to regain their weapons, then retreat behind the reception desk to look on as MICHAEL and JESSE fight.

MICHAEL and JESSE send bolts of energy across the room, singeing the walls and destroying the furniture. MICHAEL gains the upper hand, holding JESSE against a pillar. JESSE struggles to regain control, gasping for breath.

JESSE sees the team hiding behind the desk. He grins, then summons a “view screen.” A plane of red electricity slowly clarifies into a view of the asylum where the rest of the team is waiting.

 **NEEDHAM ASYLUM THRONE ROOM – NIGHT:** The scene is silent. JACK and CLAIRE stand watch. MARY, CHARLIE, and JODY are asleep. DONNA and BOBBY are sitting at the table. JACK clutches his throat. He can’t breathe. CLAIRE notices this and pats him on the back. She sees this is serious and calls to the others. They all come to see what is wrong. JACK crumples to the ground. BOBBY looks down his throat. DONNA tries rescue breaths. MARY starts to panic, screaming his name as JACK turns blue.

ROWENA

No! Jackie boy!

CASTIEL pulls SAM’s gun and fires it at MICHAEL. MICHAEL does not break his hold on JESSE, but turns his face sharply to CASTIEL, sending him reeling back on the floor.

MICHAEL

I’ll take care of you in a minute, little brother.

ROWENA takes a deep, shaky breath, summoning her courage. She steps out from behind the desk. Blue light sparkles in her palms as she recites an incantation.

ROWENA

Conteram viribus!

She shoots the blue light at MICHAEL, whose grip on JESSE falters for just a moment. It is enough – JESSE rips off MICHAEL’s helmet and grabs his face. Red lightning shoots through MICHAEL’s skull, causing MICHAEL to go completely rigid, screaming in pain.

Finally, MICHAEL crumples to the floor. A massive burn similar to DEAN’s is spread across his face, and his eyes are burned out. MICHAEL is dead.

ROWENA, CASTIEL, SAM and DEAN get up to see what happened. They look to MICHAEL’s body, then to the screen summoned by JESSE.

NEEDHAM ASYLUM THRONE ROOM: JACK takes a deep breath and sits up. Everyone is relieved. MARY embraces him.

SAM

Oh, thank God.

JESSE straightens his jacket.

JESSE

Well. It seems we’ve arrived at an understanding. You can’t hurt me without hurting your nephilim. So, if that will be all –

DEAN

It will not be all. Let Joan go.

JESSE

Why would I do that? She beheaded me, if you recall.

DEAN

You’re torturing her.

JESSE

Oh, yes.

DEAN

Why? Information? You want her to torture souls for you?

JESSE just chuckles, going to sit on a nearby sofa.

DEAN

Whatever it is, I can do it better. You can take me instead. Dean Winchester. That’s an opportunity any king of hell would kill for.

SAM

Dean!

JESSE seems interested. He considers for a moment.

JESSE

Well, look. It’s tempting, I can’t say it isn’t. But there’s something about Joan. Besides, how long did it take last time? Forty years? She’s been down there for a few weeks, her time. Twelve hours, my time, and, oh, six hours, Earth time. There’s a lot of math involved.

DEAN

(Desperate) What do you want from her?

JESSE

Submission. Complete and total, _permanent_ surrender to my will.

OBIZUTH appears in the lobby, with JOAN on her knees next to her. OBIZUTH holds JOAN by the hair.

OBIZUTH

My liege. The prisoner would like a word with you.

JOAN looks like absolute hell. Her head is cut short haphazardly. Her body is covered in dried blood. Her face is swollen so she cannot close her mouth or open her left eye. Chunks of her flesh have been cleaved from her, and all of her tattoos have been either cancelled or removed completely. The tattoos on her palms have been burned off. Her broken ribs and leg prevent her from standing.

OBIZUTH

Tell the king what you just told me. Are you ready to submit?

OBIZUTH yanks JOAN by what is left of her hair to force her to look up at JESSE. JOAN sees DEAN standing there and her mouth drops open. Her voice is a hoarse whisper.

JOAN

Dean... don’t look at me like this. I don’t want you to remember me this way.

DEAN looks like he wants to charge JESSE, or OBIZUTH, or maybe all of hell. But he knows he can’t. His voice catches with rage and grief.

DEAN

Don’t stop fighting, Joan. Ever.

OBIZUTH

Submit!

OBIZUTH throws JOAN to the floor in front of JESSE. JOAN looks up at DEAN, then right at JESSE.

JOAN

Bite. Me.

JESSE sighs, more bored than frustrated. He reaches a palm toward DEAN, who is dragged toward him bodily, unable to resist. JESSE gently lifts the hem of DEAN’s shirt, exposing his wound. JESSE very gingerly removes the gauze from the center of the wound. DEAN grunts at the removal, but cannot speak or defend himself.

JESSE

That looks pretty bad, Dean.

JESSE places one finger, gently, on the center of the wound. DEAN screams in agony. The center of the wound begins to smoke, and from the center, the red wound turns black. The blackness spreads throughout all the tendrils of the wound as DEAN cries out and tries to writhe in anguish.

JOAN

NO! DON’T!

CASTIEL grits his teeth in horror, but holds SAM back from trying to tackle JESSE. ROWENA looks on as stoically as she can.

JESSE

You have about ten seconds to submit before he dies. Then I’ll kill the angel where he stands and send the other two down to join you.

Beat, as DEAN keeps screaming and JOAN sobs.

JESSE

I’m losing patience.

DEAN forces out a word.

DEAN

NO!!

JOAN manages to lift herself up off the floor.

JOAN

I submit!

JESSE immediately drops DEAN to the floor. He clutches his side and gasps for air. He looks at JOAN and silently shakes his head, “No.”

JOAN looks directly at DEAN.

JOAN

I submit. I surrender my will. My soul. Everything. But let them go.

JESSE

Very well.

JESSE reaches back toward DEAN, but ROWENA reaches toward him first. DEAN is dragged back to where ROWENA, SAM and CAS are. ROWENA grabs SAM and DEAN and CASTIEL grabs ROWENA. They all vanish.

 

**HELL BEACH – NIGHT**

SAM, DEAN, CASTIEL and ROWENA appear on the rocky beach, right in front of the portal.

EILEEN turns around, surprised to see them appear out of thin air. Next to her, on the ground, is KETCH’s body. He is bloody, mauled by multiple hellhounds.

SAM

(Spoken) Why are you still here? You could be captured waiting for us.

EILEEN

(Spoken) I went to find Ketch. I... I found him like this. I’m sorry.

SAM

(ASL) It’s okay. We already knew.

The realization of what this means dawns on EILEEN. She seems saddened. She hands the angel blade back to CASTIEL.

EILEEN

(ASL) Thank you.

CASTIEL

(ASL) You’re welcome.

DEAN struggles to stand. Tears are streaming down his face. EILEEN, walking to the portal, places a comforting hand on his shoulder.

EILEEN

(ASL) It wasn’t a failure. You saved me. Thank you.

DEAN places his hand on hers and nods, but says nothing.

EILEEN stands in front of the portal. SAM goes to hold her hand one last time.

SAM

(ASL) I’m glad I got to say goodbye.

EILEEN

(ASL) Me too. Goodbye, Sam.

SAM

(Spoken) Goodbye, Eileen.

EILEEN steps back through the portal and disappears.

 

**NEEDHAM ASYLUM THRONE ROOM – NIGHT**

A brilliant of blue light escapes from the portal and floats up through the ceiling.

CHARLIE

Another one.

JACK

That makes 63 souls that came through the portal. But that one was alone.

MARY visibly stiffens.

MARY

Do you know who it was?

JACK

No.

With a flash of red light, CASTIEL appears at the edge of the portal, carrying KETCH’s body. His face immediately tells everyone that the mission was a failure.

DONNA covers her mouth with her hands. MARY does not hide her shock at seeing KETCH dead. CASTIEL wordlessly walks away from the portal and lays KETCH down on the floor.

ROWENA steps through next. She goes immediately to hug JACK, who returns the embrace.

Finally, SAM and DEAN emerge from the portal. SAM is helping DEAN to stand. DEAN is barely keeping it together – both the pain and the grief are plainly visible on his face.

MARY goes to help support DEAN. He sits down, gingerly, on the throne room steps.

JODY

Is Jesse dead?

SAM

No.

CHARLIE

Michael?

CASTIEL

Yes. Michael is dead.

MARY

Joan?

No one responds. DEAN breaks down in sobs, clutching his mother.

 

**INT. JESSE’S PALACE LOBBY – NIGHT**

We see a close shot of JOAN’s destroyed face. She is shivering and crying, but her face is set in determination.

JESSE

And you fully submit to me, your Dark Lord, in your will, your body and your soul, for as long as it pleases me that you should live?

A long pause. JOAN closes her eyes.

JOAN

Yes.

A single tear runs down her cheek. When she opens her eyes, they are completely black.

 

**FADE OUT:**

**THE END**

**Author's Note:**

> Hi, guys. Thanks for reading. Your kudos, bookmarks, etc are very encouraging.
> 
> I hate to leave you at a cliffhanger, especially now that I have the whole season planned out, but I'm going to have to focus on school for the next couple weeks until this semester is over. I will be back!


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